They have now failed to win their last three games, and gone three matches without scoring for the first time in almost 12 years. Not since January 2007 has there been such a drought. This was a tough night for the holders with Cristiano Ronaldo's absence starting to tell and Gareth Bale nursing a groin niggle back in Madrid.

It was a misplaced Toni Kroos pass that gifted CSKA Moscow victory. The German’s near-impeccable passing stats are as predictable as a Moscow winter but his loose ball gave Vlasic a chance he took full advantage of.

CSKA Moscow took the lead inside two minutes when midfielder Nikola Vlasic latched onto a loose Toni Kroos pass

The Everton loanee charged into the box and produced a composed finish past a helpless Keylor Navas in goal

The CSKA Moscow players go wild in the corner as they celebrate taking an early lead against the defending champions

Share this article

The 20-year-old Croatian made 19 appearances for Everton last season after a £10 million move from Hajduk Split but was loaned out by Marco Silva at the start of the season to throw Group G wide open.

The Kroos collectors item came after just two minutes. Raphael Varane headed the ball across the edge of the penalty area to Nacho and he nudged it forward to Kroos. The Germans’ idea was to send it back to Varane but it was under hit and intercepted by Vlasic who took one touch before sending it past Keylor Navas.

Madrid tried to recover quickly with Kroos doing his best to make amends for his error with a shot that was saved under the bar by Igor Akinfeev.

Vlasic wheels away after opening the scoring at the Luzhiniki Stadium in the Russian capital on Tuesday night

Twice Madrid hit the frame of the goal. First the space opened up for the advancing Casemiro and he took up the invitation for a long shot hitting the base of the post. Karim Benzema then headed on to the bar.

Real Madrid did not have it all their own way and were nearly caught on the counter-attack with Fedor Chalov twice going close.

For all Madrid’s possession they had still been sloppy with the ball and it was the Russian side who looked to have the extra gear helped by the fact that they could now play on the counter attack.

Things became worse for Real Madrid just before the break when Dani Carvajal signaled that he needed to come off. This was a Madrid side already missing Bale, Sergio Ramos and Isco. The crocked full-back switched positions with Lucas Vazquez and almost scored but there was another grimace as his shot was saved and he was replaced by Alvaro Odriozola.

CSKA fans burst into celebration in the stands after watching their team take a shock lead so early on in the game

French striker Karim Benzema looks to inspire his team towards an equaliser midway through the opening period

Nacho Fernandez tries to flick the ball on at the near post from a set piece but the Spanish side were unable to capitalise

Casemiro tries to put the finishing touch to another Madrid attack but the Brazilian couldn't make decisive contact

Ilzat Akhmetov slides into a challenge with Los Blancos playmaker Marco Asensio on the touchline in the Russian capital

Marco Asensio peppered the CSKA goal with shots at the restart but the breakthrough did not come and on the hour Luka Modric and Mariano Diaz replaced Casemiro and Lucas Vazquez.

Akinfeev had to turn one Dani Ceballos shot to safety and Modric headed wide from close range but there was a Cristiano Ronaldo-shaped hole in too many of Real Madrid’s blunt attacks.

Mariano came closest to filling it with a minute left but headed onto the post. CSKA keeper Akinfeev was sent off in injury time for dissent but it did not matter.

Madrid have not won in Moscow since 2003 when a black-gloved, silver booted Ronaldo Nazario headed in Luis Figo’s cross to give them victory. The wait goes on and so does the team’s run without a win or a goal.

Madrid boss Julen Lopetegui barks instructions at his players as they went in search of a way back into the contest